Remember to think out of the box too. I have learned great tricks from other commuters on this forum and others:

- If it's really cold (and possibly wet), no insulated gloves will work. Put on a few layers of thin gloves and a dishwashing glove (bigger than your usual size) on top to block the wind.

- If it's cold and wet, or even just really wet, no bootie will perfectly protect your foot from getting wet too. My husband and I have tried lots of them, including very expensive ones (for road riding, not for commuting though). Turns out that what the "hard core" people do (those who commute rain or shine all year and forever) is: a few layers of wool socks, a plastic bag... and sandals ON TOP of everything.

If you get a new jacket make sure it has pit zips so you can "ventilate" (especially if your commuting route is somewhat hilly).

If you need new lights, I would buy those RIGHT NOW because it's already starting to get dark later, and you never know when you'll need to stay later, be stuck with a flat tire or two, etc. I carry mine year round. Consider getting something that goes on your helmet (+ something that goes on the bike) and buying cool new reflective stickers to put... well, everywhere. THat's the fun part.

Speaking of flat tires: in the winter you don't want to have to patch a tube in the cold. Just replace it with a new one and fix the broken one in the warmth of your home.

I also love to ride in the winter, I have done it a lot (for training purposes) but this will be my first year commuting to work daily on my bike. I'm actually looking forward to cold, dark commutes. Please remind me this when December comes around!!